Job opening: Head of Sales

Full-time. Remote.

tl;dr: We've grown Tuple to millions in ARR by building an excellent product that users genuinely love. We've been closing multiple six-figure deals and are realizing there's huge opportunity on the enterprise side of our business. We're ready to hire a Head of Sales to help us close more of these deals, professionalize our sales process, and help us grow to $10M ARR and beyond.

Who we are

Tuple is an app that lets developers pair program while working remotely. Think of it a bit like super-powered Zoom screen-sharing, used by developers who are writing code together in real-time from the comfort of home.

Folks switch to Tuple because the screen-sharing is extremely high quality (important when viewing source code together) and the remote control is seamless and low-latency (important when controlling someone else's computer via the Internet).

We founded the company three years ago because we disliked the existing pairing tools, and believed that by focusing on this particular use-case, we could create a tool developers would actually like.

Turns out we were pretty much right: we've grown to millions in ARR and tens of thousands of paid users in three years without any outside funding or full-time sales help.

Want even more details on how things are going? Our CEO Ben hosts a weekly podcast where he shares regular updates.

Role overview

Currently, three quarters of our revenue is self-serve: our customers sign up, enter a credit card, invite their teammates, and start pairing. We offer them occasional support via email and ask for their feedback on new features and the product roadmap, but don't do much to help them buy. These folks tend to pay monthly.

One quarter of our revenue comes from customers who need to go through a more traditional sales process. Usually, some of their devs sign up for a trial, like the product, and then kick it over to procurement to actually purchase it. Procurement often wants to negotiate a contract and pricing, perform a security assessment, and handle billing via invoice/PO. These folks almost always pay annually, with an average deal-size of around $15k. Devs generally really like our product, so these deals tend to be less selling and more managing of the purchasing process.

So far, all our deal-flow is inbound.

As our Head of Sales, you will initially be a one-person sales department. At a high level, your job will be to turn inbound leads into happy paying customers. That could involve all of the following:

  • Negotiating pricing and other terms.
  • Reviewing contracts.
  • Filling out security questionnaires.
  • Wrangling PO/invoicing systems (like Coupa) to actually get us paid.
  • Checking in with existing customers to make sure they're happy (and hopefully interested in renewing).
  • Sharing common objections and customer issues to help shape our product roadmap.

If you perform well and we mutually think there is opportunity for more growth, we're open to the idea of expanding the sales organization. That might mean hiring an administrative person to free you up for higher-leverage activities, or perhaps hiring a success person to identify self-serve customers who should be leads for you to handle. We’re not totally sure this will be necessary, but if you can make a good case for it, we’re open to the idea.

Goals for your first few months

  • Learn the product and market.
  • Close your first deals.
  • Start to systematize our sales process.
  • Help us iterate on your compensation plan.
  • Figure out the best levers to pull to generate more deals for you to close.
  • Make us feel silly for not hiring someone like you sooner.

About you

  • You've done this sort of thing before. We want to hire someone who's already been a startup's first full-time sales person (or at least joined super early) and went on to close millions of dollars of deals.
  • You're great at creating order out of chaos. You're excited by the idea of professionalizing the sales process for a company that has a great product but has not invested in sales yet.
  • You're comfortable selling a technical product to technical people. You can talk to developers without making them roll their eyes.

Why you might want to work with us

  • We're tiny, so there are no layers of bureaucracy to work through (you'll report to our CEO/founder). You can have a very big impact on the future of the company.
  • We rarely have meetings.
  • You can work remotely as long as you're within 4 hours of Boston's time zone (EST).
  • You'll have a front-row seat at an early-stage, fast-growing company. If you hope to start your own thing some day, this could be good preparation.


We're still figuring out exactly how the comp plan should work, but you can expect something like a $125k base with OTE of $250k.

How to apply

Pitch us!

Please write something from scratch that tells us why we're a great fit for each other and what you see the future being like if we work together.

You don't need to include a resume, but that doesn't mean we're not interested in what you've done in the past. We're just leaving it up to you to tell your story the way you want to tell it.

When you're ready, email